Use of cycloaliphatic ketones as perfuming and flavoring ingredients

Abstract

Optically active isomers of alpha-damascone of formula <IMAGE> (I) wherein the wavy line designates a C-C bond of cis or trans configuration and its 3-buten-1-one derivative are new compounds having utility in the perfume and flavor industry. They can be prepared starting from an enolate of formula <IMAGE> (II) where the wavy line has the meaning given above and Me designates an alkali metal, preferably lithium or magnesium, by treating said enolate with a bifunctional nitrogen derivative of formula <IMAGE> (III) where the asterisk identifies a center of chirality; index n stands for zero or 1; each of symbols R0 and R1 defines a linear or branched alkyl or aralkyl radical, or one of them represents a hydrogen atom and the other an alkyl radical as defined above; each of symbols R2 and R3 represents a linear or branched alkyl radical, or one of them represents a hydrogen atom and the other an alkyl such as defined above; and Z designates an OH group or a divalent radical of formula HN-C(O), the nitrogen atom of which is bound to the carbon atom at position 3 and the carbonyl group is bound to the nitrogen atom at position 1; and wherein the nitrogen atom at position 1 can be optionally bound to a benzylic group of a polystyrenic resin; hydrolyzing the reaction mixture and isomerizing it by means of an isomerization agent. Cycloaliphatic ketones (I) are also prepared starting from an organo-magnesium compound of formula <IMAGE> (IV) where the wavy line has the above given meaning and X designates a halogen atom, by treating said compound with one equivalent of a lithium alkoxide.

What we claim is: 
     
       1. Method to confer, modify or improve the organoleptic properties of foodstuffs, beverages and infusion or decoction products, which comprises the step of adding thereto a flavor effective amount of (-)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one. 
     
     
       2. Method to confer, modify or improve the odorous properties of products comprising perfumes, perfume bases or consumable materials which comprises the step of adding thereto a fragrance effective amount of (-)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one. 
     
     
       3. The method according to claim 2, wherein the consumable material is a soap, a solid or liquid detergent, a fabric softener or an air or body deodorizer. 
     
     
       4. The method according to any of claims 1 to 3, wherein (-)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one is accompanied by minor amounts of (+)-(1R)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one. 
     
     
       5. The product produced by the method of claim 1, 2 or 3. 
     
     
       6. The product of claim 5 wherein the (-)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one is accompanied by minor amounts of (+)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one. 
     
     
       7. A composition comprising a flavored foodstuff or beverage which includes a flavor effective amount of (-)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one. 
     
     
       8. A composition comprising a flavored infusion or decoction product which includes a flavor effective amount of (-)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one. 
     
     
       9. The composition of claim 8 wherein the infusion or decoction product comprises one of tea or tobacco. 
     
     
       10. A composition comprising a consumable material which includes a fragrance effective amount of (-)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one. 
     
     
       11. The composition of claim 10 wherein the consumable material comprises one of a detergent, a fabric softener, an air deodorizer or a body deodorizer. 
     
     
       12. A composition comprising a perfume or perfume base which includes a fragrance effective amount of (-)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one. 
     
     
       13. The composition according to any of claims 7 to 12 wherein the (-)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one is accompanied by a minor amount of (+)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one. 
     
     
       14. A composition of a flavored foodstuff or beverage which includes a flavor effective amount of a flavoring ingredient consisting of (-)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one. 
     
     
       15. A composition consisting of a flavored infusion or decoction product which includes a flavor effective amount of a flavoring ingredient consisting of (-)-(1S)-1-(2',2',6'-trimethyl-2'-cyclohexen-1'-yl)-2-buten-1-one.